In This World of Eternal Pain
by starrily-night
Summary: He'd promised to look out for Sam. That had been his one job. He'd tried a deal, but had been refused. So he killed things, and had been dragged to Hell. He hadn't broken, hadn't taken the knife… but his baby brother was still salted and burned, somewhere out there. Alone. AU in which Dean couldn't make a deal to save Sam but he still went to Hell. Dean/Cas, not sure if slash yet.


**Okay, new AU. Hi, I'm back! I promise to update my other fics soon, but I felt like making you all have a million feels. Uh. Heh. So, enjoy this.**

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This is Dean Winchester. Fetal, weak, and almost completely unrecognizable. He has spent 240 years in Hell, and he spent his last year on Earth without his brother.

For Cold Oak was the place where the great and powerful Sam Winchester fell for good. A sobbing Dean begged and pleaded for a deal, any deal, to see his brother alive again, to prove to himself that he had not failed in his one job, but he was refused. With Sam's death and the refusal to take Dean's soul died the last of Dean's mercy, the last of his remorse. He alienated himself from everyone who loved him, the remains of his family, and set out to kill every last motherfucker left on the Earth.

Lilith was the only demon who escaped a massacre of her children and, furious, sent her hellhounds to rip Dean's soul out of his body and throw it to her demons in Hell, effectively killing the last Winchester boy.

But, even after 240 years on the rack, Dean Winchester has not broken.

And now, he is to be rewarded.

.

_You wouldn't even recognize him anymore. Three demons backed the once shining light of his soul into a corner. Even after unimaginable torture he tried to fight back with the little strength he had, clawing upwards at the demons feebly with hellhound bitten fingers._

_But someone else was watching the demons taunt. Unknown to the three and their prey, an immense creature had arrived in the Pit, a creature of light, gazing at the unfair fight in silence. If it had had eyes, it would have blinked, but the demons were gone anyway. _

_Now the broken, battered soul saw him, and cowered. He was light, blinding light of a kind that had never before been witnessed in Hell, and he feared more torture, so he pressed back into his corner. If he had had a mouth, he would have whimpered._

_The light-creature stopped, and suddenly began to form itself into a shape, a slightly humanoid shape. A tendril reached out and formed a thin hand that rested on what was once a shoulder, and the soul closed his one remaining eye, feeling a sense of bliss and comfort wash over him, despite the obvious flame licking at his body._

_._

He slammed back into a body with all the force of a train crash, force that left him woozy and disoriented for a long moment. He had no idea where he was, or who he was, or when he was- all he knew was that there was once endless pain, and now there was nothing, except a darkness that threatened to fill his soul with black. He panicked. Dark was not good.

This was a box. It had six sides. Oh, God- was he six feet under? He pushed, hard, with his feet, to no avail.

Wait. There was a lighter in his pocket. Struggling slightly, he managed to wrap his fingers around it and light it. After the initial fear of flame, the light gave him an odd sort of comfort, deep deep down in his heart.

He tried to speak. "Hello?" His voice, dry and rusty, cracked due to disuse. "Hello? _Is anyone there?_"

No answer. Feebly, he banged on the pine above his head. It crumbled away and he ended up with an unwelcome mouthful of dirt.

Scrabbling at the wood, he managed to scrape enough away to crawl out of his prison. A hand reached the sun first, and he scrambled for a grip to pull himself up. Coughing and choking, he pulled himself halfway out before he stopped, screwing his eyes shut against the sudden blinding light of the sun. But the warmth meant life, and he savored it.

He needed to find out where he was. So he slowly opened his eyes.

It was a clearing. But- no. It wasn't. He was in a grave, in the middle of what was once a forest- for all the trees were flat on the ground, as far as he could see, flat and forming a ring around the small patch of grass where his box had been.

A name popped into his head- Dean. Dean Winchester. He was twenty-eight years old, born January 24th, 1979. His mom was Mary, and his dad was John. Both deceased. He hunted demons. Okay, that was pretty out of it.

Hell. He remembered Hell. He gasped, but only barely remembered pain. It was mostly glimpses, snatches of pain. He'd gone to Hell, he'd been there 240 years- oh, God, had that much time passed on Earth? No, there'd be flying cars, Dean wouldn't have had a body. Did he have a phone? He scrambled, looking for one.

It flashed the date before dying completely. Last he remembered, it had been 2007. Now it was 2009. Okay. He was thirty. Or, perhaps 268. Two years on earth equaled 240 years in hell- but why had he-?

Oh, God.

_Sammy_.

His baby brother, four years younger. How could he have forgotten? Dead by a stab wound in the back, three years previously, by a boy with psychic powers. Granted, Sam had had them too, but… He'd promised to look out for Sam. That had been his one job. He'd tried a deal, but had been refused. So he killed things, and had been dragged to Hell. He hadn't broken, hadn't taken the knife… but his baby brother was still salted and burned, somewhere out there. Alone. The thought made him want to scream.

What did he have? He had two guns, one on his right side and one on his left, three silver knives and one wickedly curved one that could kill a demon in his boot, a leather jacket on his back, and a dead phone in his lap. He was sitting in a grave, with a wooden cross that marked it and an amulet- an amulet. His amulet. Dean reached for it, with trembling fingers.

A twig snapped. Dean whirled around, his sight clearing, and reached for the gun on his left side, a gun with a mother-of-pearl handle that was perfectly weighted in his hand. With one hand, he looped the amulet around his neck and slowly climbed to his feet.

Kill mode online.

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He made it four miles without sight of anyone, but that's when he stumbled across a large barn. Night was fast falling and Dean wanted shelter. Vaguely, he remembered a car, a beautiful shiny black baby he loves with all his heart, but she was nowhere to be found, which saddened him.

A storm was brewing on the horizon. Despite himself, Dean shivered.

He made it in the barn before the lightning crashes, and there's another crash too, on the roof, and he whirls, gun in one hand, the other hand reaching for the silver knife and the demon killing one. He had no holy water, but otherwise, he's ready for this, this thing that's been following him for two hours.

The doors flew open in a haze of smoke, rain, and sparks, and a small man in a trenchcoat strode in. He didn't look like a demon, but Dean threw the knife anyway. It lodged perfectly in the man's heart.

And he drew it back out.

Dean gulped. The man gave him a very strange look. And that was when Dean got a good look at him. Messy black hair, large, bright blue eyes- Dean felt a strange emotion boil in his chest.

"Who the hell are you?" he asked.

The man looked at him. "My name is Castiel." He said, quietly. "I'm an angel of the Lord."

"Yeah, and I'm Rudolph the frickin' Red-Nosed Reindeer." Dean lifted his gun higher. "What kind of demon can resist that knife?"

"I'm no demon." The man snarled, eyes bursting aflame. Lightning crashed and Dean saw the shadowy shape of two wings silhouetted on the wall behind him. He gulped and lowered his gun slightly. "I'm the one who gripped you tight and raised you from perdition."

"Okay." Dean said, and shook his head. "Let's assume you're telling the truth. Which, actually, I'm starting to believe. Who wants me alive so bad they send an angel down to Hell to get my broken soul? It's not like I have anything to live for here."

Castiel moved forwards. "You need to have a little faith, Dean." he said, searching Dean's eyes. "There are people looking out for you, in Heaven and on Earth. This is very important, Dean." A deep breath, as though it was the first Castiel was ever taking. "We need your help."

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**Shhhh I know it's long. I have a lot of feels okay?**

**PLEASE PLEASE PLEASE REVIEW. I LOVE YOU ALL.**


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